4-((1S,2R)-3-Benzyloxy-2-hydroxy-1-{tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamoyl}-propylcarbamoyl)-butyric acid benzyl ester | 186585-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-((1S,2R)-3-Benzyloxy-2-hydroxy-1-{tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamoyl}-propylcarbamoyl)-butyric acid benzyl ester
• CAS: 186585-82-0
• 化学式: C₆₈H₉₁N₃O₁₁
• 分子量: 1126.48
• InChiKey: SRCAMEUDMUWNHO-KXRIIEEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.54
• 重原子数：
  82.0
• 可旋转键数：
  40.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  171.19
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  4-((1S,2R)-3-Benzyloxy-2-hydroxy-1-{tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamoyl}-propylcarbamoyl)-butyric acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 水 、 溶剂黄146 为溶剂， 以80%的产率得到5-[[(2S,3R)-3,4-dihydroxy-1-oxo-1-[[2-oxo-2-(tetradecylamino)ethyl]-[2-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]ethyl]amino]butan-2-yl]amino]-5-oxopentanoic acid
  参考文献：
  名称：

  C-Fucopeptides as selectin antagonists: Attachment of lipid moieties enhances the activity

  摘要：

  The biological activity of a potent selectin antagonist could be 40-fold enhanced by attachment of a lipid moiety. Also an enantioselective synthesis of beta,omega-dihydroxyamino acids by Sharpless asymmetric dihydroxylation (AD-reaction) allowed general access to this important class of compounds. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02121-1
• 作为产物：
  描述：

  ((1S,2R)-3-Benzyloxy-2-hydroxy-1-{tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamoyl}-propyl)-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-((1S,2R)-3-Benzyloxy-2-hydroxy-1-{tetradecylcarbamoylmethyl-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-carbamoyl}-propylcarbamoyl)-butyric acid benzyl ester
  参考文献：
  名称：

  C-Fucopeptides as selectin antagonists: Attachment of lipid moieties enhances the activity

  摘要：

  The biological activity of a potent selectin antagonist could be 40-fold enhanced by attachment of a lipid moiety. Also an enantioselective synthesis of beta,omega-dihydroxyamino acids by Sharpless asymmetric dihydroxylation (AD-reaction) allowed general access to this important class of compounds. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02121-1